Late night mystery man

A random online encounter between a femboy and man leads to an evening of passion and excitement.

  • Score 8.7 (31 votes)
  • 2399 Readers
  • 1588 Words
  • 7 Min Read

After an evening out with friends, she arrived back at her hotel room feeling as if she still needed something else to fulfill her that evening.

As she started undressing out of her boy clothes, she opened her favorite app and set her status to hosting in her hotel room. Candy figured it wouldn’t hurt to look, even though it was late.

While waiting to see if any interested men were out there, she dressed in a matching red lace bra and thong. Glancing at her phone, she noticed a message waiting for her on the app. It was a simple “hello” from a faceless profile, but one with a nice dick. Candy decided this could be some quick fun, so she responded back.

As she waited for his response, Candy began reading this mans profile. Passion, kissing, body contact, and fem only. The more fem, the better. As Candy read that, her little fem clit began to swell and strain within her little red lace thong.

As their conversation continued, Candy found herself intrigued with this man. He was friendly and seemed gentle, much different from other men who only wanted a quick fuck. The more they messaged, the more that Candy continued to dress into her full fem self. She put on her long, flowing blonde wig. Pulled up some black stockings, stepped into her black high heels, and added a skirt and crop top. Fully transformed from boy mode to girl mode.

The mystery man continued messaging with all the right things. He wanted Candy to come over for some passionate fun. Though it was late, and she was getting a little sleepy, Candy couldn’t turn down the opportunity to meet this man.

He sent Candy his address and told her to wear what she had on. He loved the pics of the outfit she had sent him. She was nervous because she’d never been out in public dressed in her girl clothes. Since it was late and dark, and her hotel was quiet, she decided to go for it.

Candy pulled into the mans driveway and looked at herself in the mirror. She tossed her long hair to one side, reapplied her lip gloss, and then stepped out of the car. Though it was late at night, a streetlight still provided a little light.  Candy was filled with nervous excitement that someone may see her in girl mode, and even more excitement about meeting this man.

She knocked on the door. As she waited, she began feeling nervous. What if the man she was chatting with sent her to the wrong place? What if the man had just been playing a joke? Even if the man was real, what if he didn’t like what he saw? While Candy had the mindset of a princess, she knew she still had masculine features that many men didn’t like. She contemplated running to her car, but then the door opened.

The man standing at the door was handsome and masculine with salt and pepper hair on his head and face. He smiled at her and said, “I’m Kevin”, please come in.

Candy walked inside. Though she was still nervous, his smile made her begin to feel at ease. Kevin invited Candy to sit down in the living room. “I thought of opening a bottle of wine, would you be interested?” he asked. Candy figured a little wine might help calm her nerves a bit.

As they drank their wine, Candy and Kevin talked more about their interests and fantasies. Kevin told Candy how beautiful she looked and how pleased he was that she came over. The combination of the wine and the compliments put Candy at ease. As they continued to talk, she couldn’t stop thinking about how this man would feel on top of her. She had tuned out what Kevin was saying and could only think about kissing his lips.

“May I sit on your lap?” she blurted out, interrupting Kevin. He smiled and said “absolutely!”  Candy stood up and turned to face Kevin. She spread her legs and sat down on top of Kevin’s lap and wrapped her arms around his neck.

Kevin and Candy looked into each others eyes. The desire was palpable and they began to kiss. A few small kisses lead to more deep and passionate kisses. Kevin began to run his hands up and down Candy’s back. He whispered compliments in her ear and slowly ran his hands under her skirt to caress her butt cheeks.

“Oh daddy”, Candy moaned. “You make me feel so good!”  Kevin began to rotate their bodies until Candy was laying on her back on the sofa with Kevin on top. They continued their passionate make out session. Kevin pulled himself away for a moment and just stared at Candy. “What are you doing?” she asked. Kevin stared down at her and said “just looking at how beautiful you are.” As Candy smiled, Kevin pulled off her crop top and skirt. He stood up and pulled Candy up and led her to his bedroom.

As Candy stood up, she could see how excited Kevin was. His erection couldn’t be hidden in his shorts. She followed him to the bedroom, walking down the hall in just her bra and thong, stockings and heels.

“Lay down” he said as he motioned to the bed. Candy followed his instructions and put her back onto the bed. Kevin hovered over her kissing her lips and then began working his way down her body. She moaned as he began sucking her tits. It had been a long time since any man had been so attentive to her body and her needs. He worked his way down to her throbbing fem clit. Candy usually preferred to do all the sucking, but Kevin made her feel so amazing, she just continued to lay back and enjoy.

Kevin worked his way back to her lips with passionate making out. Candy could feel his rock hard dick against her panties. She began to move her hips back and forth to rub up against his dick. Kevin soon began moving his hips in the same rhythm. They continued to kiss and rub together.

Kevin moved down her body once again, but this time worked his tongue down to her pussy and slowly teased the outside of it with his tongue and fingers. Candy began to moan, her fem clit began to leak. Kevin continued to work his tongue further and further into her pussy. “Oh daddy, you feel so good” she moaned. “I’m glad my baby is feeling good” he replied.

“Daddy, I need you inside me” Candy said. Kevin smiled and reached over to the nightstand. He pulled out some lube and a condom. Candy grabbed the condom and threw it aside and said “No. I want to feel YOU!” Kevin got even more hard and started to rub lube on his dick and up Candys pussy.

“I’ll go slow” he said as he pushed his throbbing hard dick up against her pussy. He moved his hips back and forth, knocking up against her pussy. Candy used her hands to spread her cheeks to open her pussy. Kevin gently glided in.

Candy felt a rush of ecstasy as Kevin entered her pussy. They both moaned and resumed making out, as Kevin slowly moved back and forth. “You feel amazing” he said. “You do too, Kevin” she replied.

They both continued to move their hips in unison. Candy’s pussy continued to stretch wider as Kevin continued to grow inside of her. “You’re such a beautiful princess” Kevin said. “Thank you, daddy. You feel so good inside of me” she replied. Kevin began to thrust harder and harder as Candy continued to moan louder and louder. The sounds of passionate fucking and moaning continued to grow as the intensity of the fucking grew.

“Please fill my pussy, daddy. I need your load” Candy moaned. Kevin began to thrust even harder. He wanted to deliver Candy exactly what she wanted and needed. “I’m close!” he screamed. “Yes daddy! Give it to me. Breed my pussy!” she exclaimed.

After a few more thrusts, Kevin began pumping his load deep inside Candy. “Fucccckkkk!” he exclaimed as his seed swam out of his hard dick into her pussy. “Yes daddy!” she eagerly exclaimed as a naughty smile came over her face. Kevin made a few final pumps before collapsing onto Candy.

“That was incredible!” he told her. “You were just what I needed” Candy said. Kevin pulled out of Candy and put her thong back in place to hold his load inside her. He laid next to her and they cuddled for a few minutes.

They got dressed and walked to the door. Kevin opened the door and they embraced one final time. As Candy turned to leave, she looked back at Kevin and said “I meant what I said earlier” Kevin looked puzzled, tying to recall. “When I said you are what I needed tonight, I truly meant YOU.  You made me feel like an incredible, desirable, beautiful woman. Not just a hole”

“Candy, you are definitely an incredible, desirable, and beautiful woman. He said. “NEVER let any man treat you differently.

Candy smiled and walked to her car. She turned one last time, flipped her hair, and smiled at him. A mystery man no more, he was Kevin. A man of great passion, a great daddy, and a man that Candy hoped she would see many times again.

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